Synthesis 2020; 52(03): 353-364
DOI: 10.1055/s-0039-1691529
short review
© Georg Thieme Verlag Stuttgart · New York

Catalytic Strategies to Enantiopure Benzoins: Past and Future

Lorena De Luca
,
Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1-5/10, 8093 Zürich, Switzerland   Email: mezzetti@inorg.chem.ethz.ch
› Author Affiliations
ETH Zürich is kindly acknowledged for financial support to L.D.L. (ETH-09 14-2).
Further Information

Publication History

Received: 30 August 2019

Accepted after revision: 18 November 2019

Publication Date:
04 December 2019 (online)

Abstract

The catalytic strategies developed so far for the synthesis of enantiomerically pure benzoins are reviewed. Particular attention is given to their substrate scope and limitations. Finally, this short review highlights the advantages of more atom-economic methods that have been reported recently.

1 Introduction

2 Benzoin Condensation

2.1 Nucleophilic Carbenes as Catalysts

2.2 Homocondensation of Aromatic Aldehydes

2.3 Cross-Benzoin Condensation

2.4 Acyloin Condensation

2.5 Biocatalytic Methods

3 Organocatalytic Friedel–Crafts Reaction

4 Oxidative Methods

4.1 α-Hydroxylation of Ketones

4.2 Ketohydroxylation of Alkenes

4.3 Enantiospecific Oxidation of meso-Hydrobenzoins

4.4 Kinetic Resolution of Racemic Hydrobenzoins

4.5 Biocatalytic Dynamic Kinetic Resolution

5 Asymmetric Hemireduction of Benzils

5.1 Biocatalytic Reductions – A Brief Summary

5.2 Piers Hydrosilylation of Benzils

5.3 Photoreduction of Benzils to Benzoins

5.4 Metal-Catalyzed Hemihydrogenation of Benzils

6 Conclusion and Future Challenges

 
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